Date: Tue, 8 Sep 2009 16:33:22 +0000 (GMT)
From: sjtw69
Subject: My Brother Blake
My Brother Blake
by Stephanie Silver
Blake, my older brother, was just about the coolest brother you could ever
have. I could go on forever almost just telling about all the cool things
he thought of for us to do as we were growing up. But the coolest thing he
ever thought of was turning me into a girl.
It started out pretty innocent, I guess. Doesn't it always? Blake is about
four or five years older than me, even though it seemed like more than
that. There's a sister between us, Elise. Elise was the athletic one in our
family. She played about every sport you could imagine: basketball,
softball, soccer, lacrosse, and track. And she was good at them. So good
that she was always being invited to play on all-star teams and traveling
all over the country for tournaments.
Our dad was usually a coach or something, and since Blake was considered to
be very responsible and was old enough to babysit, he and Mom usually went
with Elise to most of her tournaments. That left Blake and me home alone. A
lot.
Blake had a creative streak, and loved to copy things he saw on TV or in
the movies. At that time, the movie "The Sound of Music" had just come out,
and Blake liked the idea of having a set of whistle commands that I was
supposed to respond to. He called it The March. Basically, since we were
expected to keep the house tidy while our parents were away, The March
involved me marching from room to room and doing whatever tasks he thought
needed to be done. Usually he would sit in a chair and direct my actions
with his whistle.
Now, before you start thinking about how abusive that sounds, let me assure
you I never felt abused or mistreated by my brother. Actually, I've never
felt abused or mistreated by anyone that I can think of. Like I say, Blake
was about the coolest brother you could ever have. Most of us kids in the
neighborhood felt honored and privileged just to be included in his
ideas. And, like I say, I could go on for hours talking about the fun
things he thought of for us to do.
So it never occurred to me that I was the one doing all the work while he
just sat there. Even now, if someone suggested that, I'd argue the
point. Yes, I worked while he just sat and watched. But that's just the way
it was. That was how the game worked. And I never felt like he was taking
advantage of me.
I guess this is a good time to point out that Blake is now CEO of a very
large and successful company, and that people work very hard for him while
he "just sits back and watches." Blake once explained it to me this way,
"Some people get paid for what they do with their hands. I get paid for
what I do with my brain."
It was around Christmas time when I was nine-years-old when Blake came up
with the idea of acting out Christmas carols. For "Little Drummer Boy" I
would march around the room pretending to be playing a drum. For "Jingle
Bells" I would pretend to be a horse pulling a sleigh. For "Silent Night" I
would lie on the floor and be as still and silent as I could.
I don't know who came up with it, but when we were growing up, we liked to
sing a slightly different version of "Rudolph the Red-Nosed Reindeer". Our
version was called "Randolph the Bow-Legged Cowboy". I won't do all the
lyrics, but basically it went, "Randolph the bow-legged cowboy had a pair
of shiny guns. And if you ever saw them, you'd pull down your pants and
run." Needless to say, it was juvenile humor.
Well, it isn't very hard to figure out how I acted out that particular
song. At the appropriate time, I would pull down my pants – usually PJs
– and run from one side of the room to the other. All to Blake's great
amusement.
It was about that same time, shortly before Christmas, that Blake was
babysitting both me and Elise one evening. Elise had a chalkboard on the
wall in her room, and Blake called a meeting to discuss potential Christmas
gifts. He had in mind to get our mother some slippers, and so he drew a
diagram of her foot, and then added a diagram of her foot being carefully
protected by a slipper. For a thirteen-year-old, explaining to a
twelve-year-old girl and her nine-year-old brother, it was very
elaborate. But that's how Blake did things. Of course the idea was
unanimously accepted, and we all pitched in our savings for Blake to
purchase the intended gift.
With that business completed, the topic turned to something of a sex
education class. Each of us, meaning me and Elise, were expected to draw
diagrams of our respective genitalia, as equally detailed as the drawing of
Mom's foot. It was a challenge, but I think we both performed admirably,
given the short notice. And I guess that's kind of where things quit being
so innocent.
I wasn't a particularly ill-behaved kid. Not at all. But as a babysitter,
Blake had rules that needed to be followed, and he strictly enforced
them. So it wasn't particularly hard to find yourself - myself, since I was
usually the only one being babysat - on the wrong side of one of Blake's
rules. The first rule I remember breaking, after the infamous sex education
class, and a few weeks after Christmas, was being slow to pull down my
pants and run across the room while acting out "Randolph the Bow-Legged
Cowboy."
In my defense, it was, as I said, a few weeks after Christmas, and I was
getting a little tired of the song. I mean... No offense to Blake, and his
otherwise admirable creative streak, but there was no variety. It seemed I
was acting out the song for him three or four times a night every night
that our parents were gone.
As punishment, Blake made me march to my sister's room. That was
tweet-tweet-twit in case you're wondering. I knew I was in trouble for not
pulling down my pants, but I wasn't sure why we were in Elise's bedroom. It
had been cleaned up before she left and no one had been in there
since. Blake sat on the bed and watched me for a minute while I stood at
attention.
Blake didn't have a whistle command for everything, of course, so finally
he spoke, telling me what to do. Of course it started with, "Pull down your
pants, Spud."
At this point I have to point out that Spud is not my name; it's my
nickname. My real name is Tate, Tate Morgan. You can imagine that Tate gets
turned into Tater, and from there into Spud.
As I said, I wasn't inclined to misbehave as a kid, so I immediately pulled
down my pants. At that point, I figured he would just have me act out the
song there in Elise's room and that would be the end of it. Blake was
strict, but he was by no means vindictive.
"All the way off," he said.
I stepped out of my pants and pushed them aside.
"Now take off your underwear," he said.
This wasn't particularly shocking. As I said, I generally acted out the
song in my PJs, and that precluded underwear, so I was naked from the waist
down when I did it more often than not. I took off my underpants and put
them with my pants. At that point I figured he'd probably just have me walk
around the house without pants for a while until he had me put on my PJs;
although I hadn't ruled out the possibility of being forced to strip
completely nude, either.
"Elise keeps her underwear in the second drawer from the top," he said,
pointing toward the dresser. "Open it up."
Okay, that was puzzling. What did he have in mind that involved Elise's
underwear? Maybe he was going to make me straighten it up. Blake liked
things neat and organized. I walked over to the dresser and opened the
second drawer from the top. There I saw Elise's underpants, in various
shades of white, pink, light blue and yellow, and all with ruffles and tiny
satin bows.
"Pick one out," he commanded.
I reached in and grabbed the top pair from the pile on the left. They were
white, with a pink bow. I held them up so he could see them. "These?" I
asked.
He nodded. "Now put them on."
Okay, that was something new. I didn't argue, though. Both of us knew,
without question, who was in charge, and it wasn't me. I just did what I
was told. I stepped into Elise's panties and pulled them all the way up to
my crotch.
That was my first time in girls' panties, and I think I knew even then that
it wasn't going to be my last. Something about it just felt right. It's
like I suddenly realized I was destined to wear panties. At least in front
of my brother.
But, okay, I'm getting ahead of myself here. It just felt... surprisingly
natural. Like, okay, I'm wearing my sister's panties. What's the big deal?
They felt nice. They felt comfortable. They felt like something, if anyone
had asked me how I felt about it, that I'd want to wear all the time. The
pink bows and ruffles? They didn't bother me a bit. I guess I had no image
of myself as being tough and macho, so it didn't bother me that I was
wearing something meant for a girl.
And that's not completely true. It didn't bother me, that's true. But I
don't want to give the impression that it didn't cause a physical
reaction. At nine-years-old, I knew a bit about sex. A bit. If nothing
else, I knew I liked that feeling of arousal I got from thinking about
sexual things. And wearing my sister's panties, I knew, was a sexual
thing. And wearing them went way beyond thinking, which meant my feelings
of arousal went up accordingly. In short... instant hard-on. All three or
four inches of it.
Blake had me wear Elise's underpants the rest of that evening, until it was
time to change into my PJs. And, of course, he didn't allow me to put my
own pants back on. I had to spend the rest of the night wearing just her
panties and a t-shirt. My erection, as small as it was, eventually
subsided, but kept coming back periodically as the excitement of wearing
girl clothes would overwhelm my thoughts and bring back those feelings of
arousal. Blake noticed that, I'm sure, but I didn't know what I could do
about it. Trying to hide it from him never really occurred to me.
When it did come time to change into my PJs, I asked him if I should
continue wearing the panties. He shook his head, and told me to put them
back and I recall feeling a little disappointed that I wouldn't get to
sleep in them.
With that in mind, the next day I purposely pushed the limits of Blake's
rules, trying to get a repeat performance of the previous day's
punishment. Like I said, I'm not a natural rule-breaker, so it took a while
before I was successful. I finally did it by not answering when he called
me to come up and wash the lunch dishes.
I couldn't keep from grinning when I heard the whistle command
tweet-tweet-twit - march to Elise's bedroom. And I think I was instantly
hard. This, the second time in less than a day that I was being punished
for willful disobedience, demanded a little more severe punishment than it
had the day before. I wasn't surprised when Blake had me strip completely
first, and then ordered me to put on not only Elise's panties, but also one
of her training bras. At the time, I didn't know there was a difference
between a regular bra and a training bra, but I knew it was a bra, and I
knew boys didn't wear them.
Once I was dressed in just bra and panties, Blake blew his whistle:
tweet-tweet-tweet-twit-tweet. I marched into the kitchen to do the dishes
I'd purposely neglected. He had me put an apron on over my sister's
underthings, but the fact that it left me fully exposed in the back to his
watchful eye only added to my arousal.
Naturally I had to spend the rest of the day wearing my sister's underwear,
and I spent almost all of that time doing whatever Blake suggested. We
played a board game at the kitchen table with me wearing nothing but her
underwear, and then I lay on the couch to watch some TV with Blake, still
wearing nothing but Elise's bra and panties.
When it came time for bed, I asked Blake if he wanted me to wear her
underwear to bed, too. He thought about it for a minute, and then decided
that what I'd done - or failed to do, actually - had been pretty bad, and
that he thought it would be a good idea if I stayed dressed that way until
I left for school the next day. He also thought that covering her underwear
with PJs might let me forget that I was being punished, so I should skip
PJs and wear only her underwear instead that night.
I looked down and nodded my understanding of his judgment, and promised I
would behave better after that. Secretly, I could hardly wait for the light
to go out so I could climb into bed wearing my sister's underwear. I think
it was the best sleep I ever had. The happiest one, anyway. I'm not sure if
I got much sleep.
For a while, that's how we did it. I would push the limits, trying to break
a rule, and then Blake would punish me by making me wear Elise's
clothes. Eventually I was wearing her skirts, too, and everything else.
That kind of changed after a few months when one day Blake said he wanted
to play house. Naturally any game you play with Blake becomes an effort in
total realism. So, when he wanted to play house, it meant we would be doing
everything he could think of to make it more real. That meant a "job" for
him as the father, and watching TV while I cooked dinner and cleaned up. It
meant housework for me as the mother. It also meant dressing up like a girl
without needing to be punished first.
And eventually, by late summer, it meant sleeping together. In the same
bed. Since I was only ten at the time, sleeping together didn't have quite
the same meaning to me as it did to Blake, who was fourteen. To me we were
still just playing house. The fact that I was being allowed to sleep in his
bedroom with him was just an added bonus. Being allowed in Blake's room
under any circumstances was, pure and simple, a privilege. Being allowed to
actually sleep there, overnight, was a dream come true. The fact that I was
wearing my sister's panties and one of her nightgowns didn't have
significance to me beyond the fact that it felt deliciously naughty. The
fact that I was doing it in my brother's bed made it feel even more
delicious.
And I guess that's where the naughtiness factor went up another notch. Not
right away, of course. It took a few months. At first we just slept
together. We didn't even call it playing house anymore. It's just what we
did when we were alone together. I would dress up in my sister's things and
stay that way pretty much until the time our parents got home or we had to
go to school.
I guess the big moment came right after Christmas. Mom, Dad and Elise were
away at a tournament, so I was sleeping with Blake. It was cold, so I was
sleeping kind of close with my back to him. I felt him keep moving his hips
and pressing against me, but I didn't know what he was doing. I thought he
was just cold, too.
Pretty soon I felt his hand on my leg, slowly pulling the hem of my
nightgown up. We'd been in bed long enough that I knew he thought I was
asleep, so I didn't say anything. He kept pulling it up, higher and higher,
until it was all the way to my hips. I squirmed a little, rolling over
slightly so he could get it all the way up. I still didn't know exactly
what he had in mind, but I knew it felt good, and I wanted to be
cooperative.
Next I felt his hand rub softly across my panty-covered ass. By that point
I was wide awake, even if Blake still didn't know it. He kept rubbing me
and touching me. I still didn't know exactly what he had in mind, but I had
a pretty good idea we were doing sex, or something close to it, so my cock
was instantly hard. I suppose if he had known that at that particular
moment, it might not have taken us so long to get to the next step.
The next day I didn't say anything about what had happened the night
before. What could I say? This was Blake, my brother, the coolest brother
ever. If that's what he wanted to do, it was fine with me. Who was I to ask
questions?
Blake didn't mention it either. And the day went pretty much as normal,
with me spending it dressed in my sister's clothes.
The next night I slept close to Blake again, and waited to see if he would
touch me like he had the night before. I even managed to toss and turn a
little before I pretended to fall asleep, lifting my nightgown up past my
hips in the process for him, just to make it easier. When he thought I was
asleep, Blake reached over and started touching me again. The touching
lasted longer this time, and he added some soft squeezes. I didn't know a
lot about sex at the time, but I knew that squeezing my butt like that
definitely crossed some kind of line. I squirmed slightly, pretending to
still be asleep. Blake's hand was instantly gone. "Shoot!" I thought to
myself. "I scared him away."
When I didn't move for a while, Blake tried again, slowly putting his hand
back where it was, and softly squeezing my panty-covered butt. I lay
perfectly still, letting him touch me and feel me all he wanted. It felt so
good. I didn't want to scare him away.
It went on like that for a few months. Each night our parents were gone,
I'd sleep in Blake's bed and let him feel me up while I pretended to be
asleep. By day, we'd both act like nothing unusual was going on. And Blake
went just a little further and further each night. At first he would run
his fingers along the waistband of my panties. Then he started casually
slipping one finger inside. Then two fingers. Then his whole hand. And
pretty soon his whole hand was inside my panties, caressing and squeezing
my butt while I pretended to be asleep.
But Blake's smart. He had to know I wasn't sleeping. I'm sure he did. And
maybe that's why he continually got bolder and more daring.
One night, instead of his hand reaching over and finding its way inside my
panties, I felt something new. It was kind of like the way he had first
touched me with his fingers, that night right after Christmas, only it
wasn't his fingers this time. Whatever it was felt like one very large, fat
finger, or all of his fingers pressed tightly together and moving as
one. It did the same thing his fingers had done that first night, wandering
all over my panty-covered bum, just touching and feeling.
It wasn't until a few nights later – and realize that sometimes those
nights were interrupted by long periods where we slept in separate beds
– that I finally figured out what it was. It was his cock. He did the
exact same things with it that he did with his hands. He ran it along the
leg openings in my panties. Then he sort of slipped the tip of it
underneath the elastic so that it was inside my panties just a little
bit. And finally he was putting the whole thing inside my panties and
rubbing it across my bare bum.
And that's when I decided to try doing something back. By that time I was
kind of curious to know what it felt like. I mean, I knew what mine felt
like. And I knew his was about two or three sizes bigger than mine. And
when he had it in my panties touching me, it always felt so hot. I mean
literally hot. As in very, very warm. I mean, it felt sexy hot, too, but
mostly I mean that it felt surprisingly warm when it was touching me. It
got to where about the only thing I could think about during the day was
his cock. So finally, I decided I just had to do something back.
I wasn't ready to admit that I hadn't been sleeping all that time, so I
kind of wanted to make it look like an accident. But I also wanted to make
sure I timed it so he couldn't get away before I had a chance to touch it
and wrap my hand around it.
So, the next time we slept together, I pretended to sleep with my hand on
the side of my leg, and then I waited until Blake had his cock up inside my
panties. When he did, I turned slightly and moved my hand down toward his
cock. Blake quickly turned and moved away, but not before I was able to
touch his cock.
For a little while that stopped the nighttime touching. It even stopped us
from sleeping together. When I came in to crawl into bed next to him, he
told me to sleep in my own room. I was hating myself for ruining
everything. I should have just kept on pretending to be asleep.
But hormones, especially teenage hormones, are demanding little things. And
Blake was almost fifteen. Eventually he said that it was okay if we slept
together again. Actually, he said it in a way that made it seem like it was
my fault, and that, if I really wanted to perform the role of being the
mother, or wife, which is really where this was headed, you know, then I
should know that involved sleeping in the same bed. And, of course, since I
was wearing girl things pretty much all the time we were alone together, it
was obvious what role I was trying to fulfill.
Back in Blake's bed, I wasn't sure what to expect. And I wasn't sure what I
should do. I was afraid to try again to touch him while he was touching me,
for fear of bringing the activity to a halt again. And, let's be honest, I
enjoyed the activity as much as he did. Maybe more. But I was also getting
just a little annoyed with the secrecy. If we were going to do it, and I
knew he was doing it, then why not just admit we both wanted to do it and
go ahead and do it?
Because admitting to him that I hadn't really been sleeping all that time
would have been a confrontation, and it was easier for me to just go along
with whatever he wanted. So I kept pretending to be asleep.
And for at least two more nights, nothing happened. At least not anything
that I was aware of. Maybe he was still doing it, but was waiting until I
really was asleep.
Or maybe, like me, Blake got tired of the secrecy too, and decided to bring
it out in the open. He could do that. All he had to do was come up with a
new idea, and new game for us to play, and I'd go along with it. I don't
know if he knew that. I don't know if I even knew that. In hindsight I know
it was that simple.
The game he came up with was... You know what? I don't know what you'd call
it. It was a combination of games. Sometimes it was Truth or
Dare. Sometimes it was Spin the Bottle. Sometimes it was Post Office. One
time it was a game called Seven Minutes in Heaven. And sometimes it was
just dancing. Yes, dancing.
Being in ninth grade, Blake had started going to teen parties, and doing
other teenager activities, and so he started knowing about all these
different games and activities that teenagers did at their parties. So I
guess the game idea he came up with was to role-play that we were at a teen
party.
Of course, I was only ten, so... pretending to be a teenager at a party
took a lot of imagination. Of course, I not only had to pretend I was a
teenager, I also had to pretend I was a teenage girl. Blake helped me, of
course. And he never got upset if I struggled a bit with my role. He would
simply tell me how I was supposed to do it, and then let me try again.
As you can imagine, I got rather accomplished at knowing how to be a girl
at a party. Armed with that knowledge, you can just imagine how my first
real teen party went. But that's another story. Or maybe it's the point of
this one. I don't know. All I know is it's kind of getting me off-track for
now.
So, back to the imaginary parties with Blake. As I said, it also involved
dancing. Blake would start off by putting on some music – he had an
extensive music collection – and then we'd pretend we were at a
party. Naturally, according to Blake, boys and girls started dancing when
they were at parties and they liked the music, so he said we needed to do
that.
Part of Blake's genius, I think, is that he can suggest an idea, and make
it seem like the most natural thing in the world to you. As if you would've
thought of it yourself, if you'd had a little more time. That's how it was
with the dancing. We almost HAD to do it. He literally had me thinking it
was my duty to dance with him.
What he said was that first, he actually was a teenage boy, and therefore
needed to practice dancing whenever possible. See how he made me feel like
it was not only a game we could play, but also a duty I owed him? Second,
he said, was that I would be a teenager too, some day, and therefore needed
to learn how to dance. Okay, more of his genius at work here. See how he
shades the half-truths? Yes, he taught me how to dance fast songs, and that
knowledge would be valuable to me later, just because it wasn't gender
specific information. What he didn't mention was that I'd also be learning
to dance slow songs, and that I'd be learning those from the female role.
So, we started dancing. First the fast songs. Of course I'd be wearing an
appropriate party dress or cute skirt while he taught me how to do it. I'd
also be wearing Elise's high-heels. So I ended up learning how to fast
dance in a skirt and heels. I think if you learn to dance in a skirt and
heels, dancing in jeans and flat-soled shoes is a piece of cake. Of course,
by the time I got to the point where I might have danced as a boy wearing
jeans and flat-soled shoes, I'd pretty much become a full-time girl,
socially at least, and probably would have found that role equally awkward.
But I'm getting ahead of myself again.
So that's where things were for a long time. And I promise I'll get back to
the teen party role-playing stuff in just a second. There was still the
sexual touching at night, although that changed slightly. I suspect the
pretend party playing had something to do with that. In frequency, it was
occurring less and less often. On the other hand, Blake didn't seem as
intent on keeping it secret. He would generally wait until he thought I was
asleep, but if I woke and caught him with his hand, or something else,
inside my panties, it was no big deal. He'd just keep on doing what he was
doing.
And maybe that was also due to something else that started happening about
that time. TV. If we weren't pretending to have a party, we would sit next
to each other on the couch and watch TV. Or lay side by side. Front to
back, actually. We had pretty much stopped calling it "playing house" by
that time, though. It was still the same game, I guess, but it had just
turned into what we did when we were together and it was just the two of
us. I was the wife and mother; he was the husband and father.
And, that's not quite true. It was all these things sort of happening at
once, and it's hard to say which one was responsible for the other. It was
the sleeping together, and pretending we were married, and practicing for
parties. And each seemed to have an effect on how we did the others. What
I'm getting at is the husband/wife game was sort of evolving into more of a
boyfriend/girlfriend relationship.
Now, back to the pretend parties, because that seemed to me to be the
center of all the other changes.
After a month or two of dancing fast songs, and sitting out the slow songs,
Blake said it was time to try slow dancing. For someone who was using me as
a practice partner for real parties, he seemed to know an awful lot about
how it was to be done. That shouldn't surprise you if you know Blake at
all.
We started with the basic steps: the fox-trot, the waltz, and the
two-step. "Nobody's ever going to dance the fox-trot or the waltz with
you," he said, dismissing those almost immediately. Of course, he did have
me learn them "backward" in heels first, so when they tried to teach them
to me in school a few months later, I was constantly getting it mixed up.
We spent more time with the two-step. I call it the two-step. Blake didn't
have a name for it. He just said, "This is the dance you'll use all the
time." For all I know the two-step is something else. It's just your basic
dance step when you're not really trying to do anything more than move your
feet without stepping on each other's toes.
He first taught me the "proper" variation: the one where he put his hand on
my waist, and held my right hand in his, and we stayed approximately six
inches apart. "This is the way most guys will dance with you," he
said. Yeah!, He really did say that, because I remember thinking that he
was just teasing me at first – he knew I wasn't going to be dancing with
any guys other than him. Didn't he? But when he showed no signs that he was
only teasing, and started talking about something else as if he hadn't said
anything odd, it made me wonder.
After that, he taught me the other ways to dance: the not-so-proper
ones. First he taught me the version where the "six-inch rule" gets
ignored. Then he showed me the variations of the bear-hug, starting with
hands held loosely around each other's waist, followed by the alternate
method of his hands around my waist and my arms around his neck. That, he
said, was the way couples danced when they wanted to show that they were
"exclusive". And then he had to explain to me what exclusive meant.
And that last one was the one we used from then on.
According to Blake, parties also included games, so we had to start playing
those. We played commercial games, like Twister. And, of course, I played
it wearing a skirt. We played card games, including poker. We also played
non-commercial games, like Truth or Dare. Blake modified the rules
though. I guess you'd say that he modified the rules to his advantage. But
I wasn't exactly complaining.
Blake's rules for Truth or Dare were mostly one-sided. I got to choose if I
wanted to answer a question, which he tried to make embarrassing for me, or
do a dare. I never asked him questions, and I never dared him to do
anything. The dares usually involved me taking off my clothes, or, if I
hadn't yet put on girl clothes, changing into something of
Elise's. Sometimes the dares would involve doing other typical party
activities, such as dancing. They were really just an easy way for him to
suggest things for us to do. A few times they would involve more risky
activities for me, such as going outside dressed as a girl, or calling and
ordering a pizza and telling them a girl's name when they asked for my
name.
It was a dare that finally brought the sexual touching out of
secrecy. Since we had started dancing with each other, and pretty much used
only the "exclusive" method of dancing where I had to put my arms around
his neck while he put his arms around my waist, he could dare me to do that
quite easily. And then, while we were dancing, he could continue the game,
making me answer embarrassing questions or do dares. The dare that finally
brought the sexual touching out of secrecy came after we were already
dancing, and I chose dare again.
"I dare you to let me put my hands on your butt."
Well, I was already letting him do that to me at night, so it wasn't much
of a dare for me. Plus, I didn't argue with Blake. I just did whatever he
said. So with barely more than an "OK" from me, his hands slid down to my
bottom.
"This is the way couples dance when they really like each other," he said.
I nodded. It felt good. It had always felt good to me. And I liked that I
didn't have to pretend I was asleep. "It feels nice," I said, acting as if
I'd never felt his hands there before.
I have to remind you that I can tell this story a whole lot faster than it
really happened. The actual pace of events was moving at what I would call
glacial speed. Kind of imagine that between each paragraph I write, there's
a week or two where nothing new happens. On the other hand, I'd have to say
that things never went backward. Once Blake openly put his hands on my
butt, or did something else, there was no need to "re-introduce" that
particular action into our activities later. It was automatically assumed
and allowed the next time.
So, the touching dares escalated each time. The first time Blake dared me
to let him touch my butt through my skirt. Then he dared me to let him put
his hands under my skirt and do it. And then, probably because it's hard to
dance with someone's hands inside your panties, he started daring me to
pull up my skirt while we watched TV and let him touch my butt that way.
Eventually he even had me take my panties all the way off, as a dare, and
then followed that by daring me to let him touch my butt.
We started kissing more by accident. If you can call anything Blake does an
accident. It happened while we were dancing the dirty way, with his hands
up under my skirt, I remember thinking how good that felt, and how much I
actually liked pretending to be his girlfriend. As far as everyone else was
concerned, I was still a normal boy, but with Blake, I didn't even pretend
to be anything else. I was his girlfriend. At least, that's how I saw it.
I knew a little bit about kissing. I knew it looked sexy in the movies, and
I thought it would feel sexy to have my lips touching someone else's. But,
still in grade school, I'd never done it with anyone. And I wasn't exactly
thinking about it just then. But Blake was.
At that time Blake was taller than me by several inches. Fortunately,
Elise's high heels made me only a few inches shorter, so when we danced, I
usually just put my head on his shoulder and enjoyed being touched by
him. It was while we were doing that that I felt him turn his head slightly
and kiss my neck.
I kind of froze. What was that? I mean, I knew what it was, but was it
really what I thought it was? I didn't know. The next kiss landed on my
cheek. Well, if Blake wanted to kiss, I was all for it. I turned my head
slightly and kissed him back. I don't know how many kisses it took for our
lips to touch. Probably three. it seemed like more. It seemed like six. And
then, when our lips finally did touch, I'd estimate the kiss lasted no more
than a millisecond.
But we'd done it. We'd kissed! And, like I say, once a bridge is crossed
with Blake, there's no need to go back to cross it again.
The second kiss lasted closer to a full second. It came approximately
forty-five seconds after the first one, just long enough for each of us to
kiss our way to the other side, wait a discrete amount of time, and then go
back. Only this time, when Blake's lips touched mine, neither of us was in
a hurry to break it off.
That's when we started playing Post Office, the kissing game. Here's how we
played it. Blake would think of five girls he knew and write each of their
names on a sheet of paper. Some of them I knew; some of them I didn't. If I
didn't know them, he would describe them too me. He had to describe them
because my job was to act like I was them when their name showed up during
the game. For my part, I had to think of five guys who I thought were
"cute" or attractive, and write each of their names on a separate piece of
paper. Then the "post office" would juggle the names around and put a
girl's name in an envelope with a boy's name. When it was time for a letter
to be delivered, we'd open an envelope and see who the names were.
At that point, I'd have to act like I was that girl, and Blake would act
like he was that boy. Since the girls Blake was choosing were closer to his
age than to mine, and consequently well-developed, we decided (Blake
decided) that I needed to start putting something in my bra cups to make it
look like I had breasts.
He actually came up with a mixture of bird seed in an old nylon stocking
that he said felt very realistic. With the knots on the stockings turned to
the front, we could even make it look like I had nipples. I confess that I
was being educated, because I didn't know how much bigger girls' nipples
were, on average, than boys'.
Oh, and one other thing I should mention here, because I'll forget about it
later. Every time we played the game, my list of boy names had to
change. His, of course, was allowed to stay the same, although, in
fairness, he changed his quite often, too. I was allowed to keep a current
"crush" or two on the list, but it couldn't be the same list as I'd used
previously. Along with the names, I also had to write down two or three
things about each boy that I found cute, or sexy, or attractive.
The intention, I guess, was that I had to start thinking about boys more,
and I had to start thinking about them the way a girl would. I've probably
mentioned this before, but it keeps coming up that, as all these things
were going on, it would occur to me that Blake was slowly turning me into a
girl. I was quite literally losing my ability to be a normal boy. My way of
thinking was changing. I was starting to think more and more like a
girl. In some cases, those instincts, the feminine ones, were becoming my
first instincts. If I was fortunate, I would catch myself before making a
fool of myself somewhere. If I wasn't so fortunate, I'd draw curious looks
from people.
And I guess I should add that about the only time I felt really comfortable
with my dual sexuality was when I was alone with Blake. With him I didn't
have to worry about making a mistake. And, yeah, with him, I was probably
– undoubtedly - behaving more like a girl than a boy.
The first name we drew was Cheryl Nokes. I knew Cheryl. She lived
nearby. Cute, bubbly personality. Very pretty. Very, very well endowed. At
least a D-cup. And naturally there was no way to pretend I was Cheryl
without stuffing something into my bra. And that was the first time I wore
a bra with breast forms. It wasn't the last. And, I'll admit it. I loved
– absolutely loved – having tits. Can I say they just felt right
without feeling like I'm repeating myself?
So, pretending I was Cheryl, I sat on the couch next to Blake, who was
pretending to be Phillip Moyer. Phillip was from my list, of course. I
picked him because he was quiet, but nice looking. Well, I thought he might
be nice looking. I mean, he was, but at the time, I still wasn't exactly
sure what I looked for in guys as far as looks. But, whatever it was, or
is, Phillip had it. He was cute. Kind of a soft, shy grin, gorgeous brown
eyes, medium brown hair with a bit of a flip to it. So I sat on the couch
as Cheryl, preparing to make out with my brother who was pretending to be
Phillip.
Truthfully, I didn't really know what to expect. I knew we were going to
kiss. That's about it. After that, I just planned to do whatever Blake told
me to do. I hoped it would be sexual.
It was. Well, it wasn't, but... that kiss! I knew about French
kissing. And after a minute or two... No, it was actually nowhere near that
long. It was after probably about six seconds or so of kissing with our
lips closed that I felt Blake open his mouth. I think I knew what that
meant, and I knew what to do. I must have, because I automatically opened
my mouth and let Blake stick his tongue in my mouth. French kissing.
I liked how it felt to have his tongue in my mouth, moving all around,
touching my teeth and stuff. And then it was my turn to stick my tongue in
his mouth, and I liked how that felt too. I mean it was like the most
intimate thing I could imagine doing with another human being. At least to
that point. I was going to learn more.
French kissing led to making out, with Blake's hands pretty much going
anywhere they pleased. Mostly that meant on my ass. He liked touching my
ass. A few times he would reach in front and play with my dick, too. And I
really liked that. If I'd had my choice, we would have done that all the
time.
And so, one time, after he'd touched me there, I decided to return the
favor. Of course, his dick wasn't as easy to get to as mine was, since I
was wearing a skirt and panties, and the skirt was generally up around my
hips shortly after we got started. His was buried in layers of fabric from
jeans and boxer shorts. I wasn't sure if he would want me undoing his
pants, or reaching inside, so I just touched it through his pants.
I won't say I was surprised at how big it was. Maybe a little. It was
bigger than mine, that was for sure. And it was definitely hard and
swollen. Maybe that's what surprised me. To that point, I'd really only
felt it touching my butt at night, or indirectly when we made out and I
felt it pressing against my leg or something. So when I felt it, when I
felt this long, hard thing in his pants, and knew that he was as aroused as
I always was from making out, that's what surprised me.
I kind of got cock-hungry after that. I'd keep thinking about how big it
was, and how it had felt to touch it, and I'd just want more. Since Blake
hadn't told me I couldn't touch it, I started touching it all the time. It
didn't take very long before he started wearing some loose-fitting shorts
to our make-out sessions, and I was able to reach inside and actually touch
his dick and hold it in my hand.
The stuff at night started happening more after that. He always wanted to
touch my butt, and would usually have me lay on my tummy while he fondled
me. I didn't mind. To me, it just felt good. Sometimes he would have me
sleep without panties, and would make me press my bare butt up against him,
so that he could press his dick into my butt crack. I didn't mind that
either. It felt good.
Sometimes when we watched TV during the day, he would have me lay on the
couch on my tummy while he sat on top of me with his pants all the way
off. I knew it wasn't sex, but I knew it was getting really close.
One night when we were in bed, and I had my bare butt pressed up against
him, Blake started humping me. I didn't know exactly what was going on. It
was different, but it didn't hurt or anything, so I didn't say
anything. Suddenly he pressed really hard against me and said, "Oh shit!"
and I felt something warm and wet spreading all over my butt.
I didn't know about cumming, so I thought, because of the swear word, that
something bad had happened, and I thought the warm, wet feeling must be his
blood. I really thought I'd broken his dick in half or something.
I turned around to see what was the matter, although I couldn't see much in
the dark. "What happened?" I asked.
Blake seemed embarrassed at first, and that just made me more sure that his
dick must have broken in two somehow, and that he was embarrassed to show
me. "Is it broken?" I asked, automatically reaching my hand toward him.
He grabbed my wrist, stopping my hand from reaching him, and said "No."
"Are you bleeding?" I asked.
"No."
And then suddenly he started to laugh. "You don't know what happened, do
you?" he said, stating the obvious.
I felt my cheeks burn red. "No."
He released my hand, and guided it to his slowly shrinking erection. By
that time I knew how it felt when he was aroused, so I was puzzled what had
happened to make it small again. Plus there was still some wetness on the
tip. And a strong smell of cum that I thought was a chlorine smell. I
really had no idea what was going on. I still imagined the wetness was
blood; I was sure the sheets were nothing but a bloody mess.
When I didn't say anything to show I knew what was going on, he finally
told me, "I came, Spud. I came on your ass."
Well, that didn't exactly clear things up for me. I'd never heard that verb
used that way before. Blake wasn't in a mood to explain, however. He just
wanted to sleep. I lay there a few minutes, feeling the wetness on my
bottom slowly drying and cooling. It felt uncomfortable, so once I heard
his breathing changed, and was pretty sure he was asleep, I rolled out of
bed and went to the bathroom to see what happened.
Of course, other than a weird stickiness that had dried into a clear film,
there was nothing to see. Still confused, I went back to bed, after taking
a moment to find the panties I'd been wearing earlier in the
evening. Putting them on just seemed to make me feel better and slightly
less confused. After lying sleepless for a few more minutes, thinking and
trying to figure things out, I finally fell asleep.
The next night, with our parents and Elise still gone, Blake gave me a sex
education class. He explained what cumming meant, and what cum was. He
explained how, if a boy squirted his cum into a girl's "cunt", it could
make her pregnant. He also explained that, since I wasn't a real girl, I
wouldn't get pregnant. It was all the things you kind of wonder about as a
kid.
We finished the class with a demonstration of a hand job. He said some guys
had to make themselves cum that way, and that when they did, it was called,
among other things, jerking off. But, he added, it was always better if
someone else – meaning me – could do it for you. He didn't
demonstrate it then, but the best way of all, he said, was to have it
happen by rubbing your dick on a girl, or by having it inside a girl's
vagina. "That's called fucking," he said with a certain reverence that
struck me as odd, because I knew about the F-word.
Well, since I didn't have a vagina for him to stick his dick in, we settled
for hand jobs and rubbing his dick on my butt. He usually came at some
point, so I got used to having his cum on my hands or on my butt.
Eventually he wanted to try something that he said was closer to what it
would be like if I really was a girl and he wanted to fuck me. He had me
lie down on my back and hold my legs tightly together while he fucked the
space between my thighs. Usually when he did that, he liked to pull out
just before he came and squirt his cum all over my dick and balls. Other
times he would squirt it in my crotch, and I would feel the wet, stickiness
of it between my legs. Another variation was to do the same thing, but with
me lying on my tummy. But we liked it best with me on my back because then
we could kiss and make out. And if I was wearing a bra, with the cups
stuffed, he said it felt just like he was fucking a girl.
I was twelve and going to junior high when Blake suggested that, instead of
using my hand to make him cum, I use my mouth. I wasn't sure I wanted his
dick in my mouth, so I hesitated. That's where his pee came out. But Blake
was insistent.
And persuasive. He reminded me that I didn't have a vagina, so I couldn't
fuck the way a "real girl" would, and so it was my duty to be creative. I
resisted the temptation to ask him why that was my duty – I knew,
because most girls weren't getting pregnant, that there were a lot more
girls in the world who weren't having sex that way than were.
I resisted for two reasons. One, I just didn't argue with Blake. From
experience, I knew that, no matter how right I was, he'd be able to win any
argument. He was just better at defending his opinions than I was.
The second reason was that I liked what we were doing, and had no real
interest in pointing out an error in his thinking. Doing so might backfire,
and cause him to find someone else to play with. With nothing to gain by
arguing, and much to lose, I didn't really care if his arguments didn't
always make sense.
Blake was insistent that I at least try sucking his dick once. If I didn't
like it, he said, I could quit doing it. And, like I say, he was
persuasive. He made me feel like I had to do something extra to compensate
for the fact that I wasn't a real girl.
We arranged that first time for an evening when our parents and Elise were
gone. It was, I think, the furthest in advance we had ever planned
anything. I remember as they were packing things into the car earlier in
the day, knowing that the "big day" had actually arrived. I was going to
suck Blake's dick just as soon as they were gone. We'd been planning it for
days. There was a big S on Blake's calendar, and he would make sure I saw
it there every day.
We started that special evening off with our usual game of Truth or Dare. I
didn't bother picking Truth, because I knew we just wanted to get straight
to the dare.
The first dare was for me to put on Elise's underwear and to stuff the
cups. No skirt or blouse this time. Then Blake had me walk around the house
for a while in just her underwear. He kept telling me how sexy I looked,
and assured me that I looked just like a girl. For some reason that made me
happy. I'd grown to like being a girl, and took pride in looking as much
like one as I could.
While I walked around pretending to be a girl walking around in her
underwear, he started to tell me how horny he was getting from looking at
me, and then let me feel how hard his dick was through his pants. He kept
doing that, and taking his clothes off a little at a time, letting me feel
each time how hard I was making him, until I was as aroused and horny as I
can ever remember being.
Finally it was time. "I dare you to suck my dick," he said, knowing I would
do it.
By that time he was completely naked, which actually didn't happen very
often when we played. We went to the bathroom, and he washed himself
thoroughly with a wash cloth for me. And then it was time. I looked at his
huge dick, knowing I had to suck it.
I'm afraid I don't remember much about it, to be honest. I just put my
head down, opened my mouth, and it was in. I remember thinking it felt kind
of cool to have his dick inside my mouth. It felt so naughty and nasty. But
I don't remember much else about it, like what it felt like to rub my
tongue along the smooth head, or up and down his shaft. It was just in my
mouth. That's about all I remember.
Well, the need to wash it diminished rapidly after that. I think he did it
the next time, and maybe once after that, but in almost no time he was
simply pulling down his pants and I would start sucking. Of course he'd
usually dare me first to do it.
With his help, I got better. He taught me things to do to make it more fun
for him. He taught me to look at him while I did it, so he could see it
going in and out of my mouth. He had me wear Elise's lipstick a few times,
and said that really made him hot to see my red lips wrapped around his
cock. He taught me to go deeper by relaxing my throat.
The summer I turned thirteen, Blake told me he wanted to cum IN my
mouth. I'd had his cum all over my body, so I was pretty much used to
it. And Blake had started several months earlier getting me used to the
taste of cum. At first it was just a taste. He would dare me, after he
came, to just taste it, or just put a little on my tongue. And then he
would dare me to put some on my tongue and close my mouth. and then he
would dare me to swallow a small amount of his cum. And eventually I was
licking up as much of his cum as I could get and swallowing it for him.
And he told me that's what "good" girls did for their boyfriends.
So letting him cum in my mouth wasn't a big deal It was just different. I
had to suck longer, and then... Well, I'll admit when it squirted into my
mouth that very first time, that was a big deal. Actually, it's still a big
deal to me when a guy cums in my mouth. I like it. A lot. But, I guess I'm
getting a little off-track again.
I knew he was cumming. I felt his dick twitch, and I felt the jets of cum
shoot out. I kind of stopped sucking, and just kept it in my mouth. I
remember there was lots of saliva, and then I started thinking there might
be more saliva there than normal, and then I kind of noticed the smell
filling my nostrils, and the consistency of what was in my mouth was a lot
thicker than my normal saliva, so I knew it was Blake's cum.
He made me open my mouth and show it to him before having me swallow
it. "That looks so sexy," he said. But he didn't offer to kiss me.
I guess that, during the next year, about four things happened. First, I
learned a lot about my sexuality. I learned that I was a lot happier being
the "girl' in a relationship than I was being the boy. My
friends... Actually, I wouldn't call them friends. I was kind of a loner,
to tell the truth. But kids my age that I knew, like Phillip Moyer and
Bruce Rowan, had started liking girls. I still felt very uncomfortable
around them.
And yet, I liked looking at them, and thinking about them. It just occurred
to me one day, as I was sneaking peeks at Debbie Walker's tits during
Sunday School class, that I would rather be the one being peeked at than
the one doing the peeking. It occurred to me that what I would really like
is to be Debbie Walker, and have tits, and have boys looking at them and
getting aroused by them. Not that I wasn't aroused, but... I just realized
I'd be happier being on the other side of that arousal.
And so I started looking at girls differently for a while. I started
studying their mannerisms, the way they dressed, the fashions, their
makeup, and, of course, their lovely and sensuous bodies. I started
imagining how my life might be different if I'd actually been born a girl.
Of course, thanks to my brother, I was already looking at guys in a
different way. I knew which ones were cute, and why. Gym class was my
personal nightmare. I was so afraid of "popping a boner" at the wrong
time. One time, Dave Lizakowski got caught with an erection, and no one
ever let him forget it. He was branded a "faggot" for the next two years.
Somehow I managed to go undetected. If I hurried, I could get in and out of
the shower before the more "manly" boys, like Jon Taggart, Tom Willard, and
Scott Miller got there. They were the ones that, physically, most reminded
me of Blake, and I knew if I spent too long thinking about any one of them,
my dick would respond by sticking out. Of course, once I was sure I had
everything safely concealed, I wasn't above sneaking a peek at them too.
The second thing that happened is that Blake started liking girls, too. To
the point of getting a girlfriend, Patti Talbert. Patti was pretty. Cute. I
loved her short hairdo and her striking brown eyes. And she was well
endowed. And, I have to point out here that, no I don't have an obsession
for large breasts. It just happens that all the girls I've felt the need to
mention in this story have been that way. My actual preference is for
slightly smaller breasts; a Bcup to me is just about the perfect size. As
Blake's little brother, Patti was nice to me, offering to cut and style my
hair and telling me funny stories that involved doing amusing things with
her tongue.
And second thing and a half, I guess, is that Blake got a job and started
working, so there was a lot less time for us to be alone together. Just
when I was starting to figure out who I was sexually.
The other two things were not unexpected, but they seemed to be the most
tragic of all. The first one was puberty. Mine. Hair started growing in
what I considered to be all the wrong places. I knew what girls were
supposed to look like, of course, and hairy legs and hairy underarms were
definitely not it. It wasn't enough to require shaving regularly, but there
was even the start of facial hair. I was devastated. At first I tried
shaving away the body hair, but I knew that wasn't going to solve the
problem. Eventually someone, my parents, were going to wonder why I was
shaving my legs. No, I realized, puberty was going to win the battle, and
turn me into a boy whether I liked it or not.
And trust me, I didn't like it.
And finally, the last change, the one that was probably the hardest of all,
was that Blake left for college. I think, if he had been there, I might
have been able to handle the other things. Without him, I felt lost and
alone.
I don't know what I can say about those four years. They were lonely. They
were easily the worst four years of my life. I was... I wasn't suicidal,
actually. I was sad and depressed, obviously, but I always felt like there
was an answer out there somewhere, and all I had to do was find it. But I
didn't know where to look.
There was one class, cooking class with Mrs. Taylor, that made me feel at
home for a short while. Home Economics for boys was kind of a new idea;
Home Ec classes were pretty much a girls' class until then. But once I
heard that a few guys on the basketball team had taken it the year before,
and a few of my friends were willing to sign up with me, I wanted to give
it a try. In my four years of high school, it was the only class that made
me feel "happy" again. It was like for that one hour, I could safely
pretend that the apron I was wearing - in jest, of course, and partially at
Mrs. Taylor's behest - was really meant for me. For one hour I could be who
I wanted to be. Within limits, of course.
Summers were a little better. I would have sex with Blake a few times, when
he wasn't busy with something else. And, of course, there were the few
holiday weekends when he would come home from college for a few days. Those
times didn't include sex very often, though, because we could only have sex
when our parents were gone, and if they were going to be gone for the
weekend with Elise, Blake would usually wait and come home some other
weekend when they would be there.
I was, however, left on my own a lot and I spent a lot, most, of that time
wearing Elise's things.
When I could, I would tell Blake how I felt about puberty, and my
disturbing loss of femininity. I would tell him how much I liked the games
we played where I dressed up like a girl, and how, if I could, I would go
back to those times and never leave them. They were few, but when we
talked, I poured my whole heart out to him.
And he understood. He understood in a way that only Blake could. He said he
would figure something out, something that would make me happy.
And I knew he would. He was Blake. He was the coolest brother you could
ever have.
* * * * *
During that time Blake encouraged me to express my femininity wherever I
could. He asked me to write him letters using the most feminine stationery
I could find. I even found a pink-ink pen that I could use. He encouraged
me to write as if I was a girl, writing to her boyfriend. And as the years
passed, I enjoyed seeing my handwriting slowly change from a boy's scrawl
to a young girl's loops and curves.
The style during my high school years was for boys to grow their hair long,
and Blake encouraged me, despite our father's objections, to let my hair
grow long. He said it would help me feel more feminine, and it did. By the
time I graduated high school, it was down past my shoulders.
Of all the sexual things we did, I guess I never mentioned anal sex. We
tried to do it once, just before Blake left for college. I was only
fourteen. I knelt down, naked, while my brother got behind me intending to
enter me that way. But after only one or two tries, it became painfully
obvious that his big dick was never going to fit. And so we gave up,
settling for blow jobs and hand jobs instead.
After four years of college, Blake graduated magna cum laude in
engineering. Before he even graduated, he had several job offers, including
one from a large corporation in Tucson, Arizona. That's when things finally
started to change. At the same time, I was just finishing high school, and
trying to decide where I would go to college. I applied at the two local
colleges, and at two other colleges further away, including the college
Blake had gone to. If I could, that's the one I most wanted to go to.
Blake, however, had a better idea. As soon as he knew he was moving to
Tucson, he had me start thinking about going to the University of
Arizona. That way I would be able to move in with him. We didn't discuss
what that would mean exactly, but after four years of being away from each
other, I wanted nothing else.
The first step was for me to convince our parents that I wanted to go to
college in Arizona. That took some effort, because I hadn't put it on my
list until Blake told me about it. Actually, I think they understood how I
could have missed it. I'm sure they knew just how much I wanted to be close
to Blake.
In the end, that's what made it work. Since going to Arizona meant paying
out-of-state tuition, it was going to be more expensive. By living with
Blake in his apartment, and not paying room and board, the difference was
in favor of me going there. Of course that was asking a lot of Blake, who
generously agreed to help the family out.
Blake also came up with some non-finance-related reasons, telling our
parents that leaving home would be good for my education, and that
employers valued the maturity that comes with living away from home. And so
I became an Arizona Wildcat.
Officially I had my own bedroom at Blake's apartment, the one in the front
by the stairs. Officially. Unofficially, we used it for studying and as a
storage area. I think we both knew, as soon as I moved in, that I would
never sleep there. Blake put a fold-away couch bed there, and if anyone
ever asked, that's where I slept. And that's where I kept my boy
clothes. But even as we were making the thirteen-hour drive from our
parents' house to Blake's with all my things, Blake suggested I plan on
spending my time at home dressed as a girl. "I know I'll like it," he said,
"And I think you will too."
That was something of an understatement.
My immediate problem, however, was clothes. Like any other cross-dresser, I
had a few things that I'd collected over the years. Not very much, for fear
of discovery. But I did have a few things, and knowing that Blake would
allow me to wear them – in fact, would probably insist on me wearing
them – I had brought them along. It was either that or throw them
away. And I couldn't bear to do that.
My collection of girl clothes included a string bikini I'd held on to one
summer when Elise got a new one. I don't know if she ever missed it, or if
she ever wondered where it had disappeared to. For nearly three weeks it
had lain in an unclaimed pile of clothes near the washer, until I finally
picked it up and hid it in my drawer. I also had a black flowered baby-doll
night gown and several pairs of panties that I had obtained in much the
same way, picking them up when they went unclaimed for a few weeks.
Knowing I would need a larger wardrobe if I was going to live in his
apartment full time as a girl, Blake started right away daring me to buy
things. Since I didn't have a lot of my own money, and what I did have was
earmarked for school, Blake offered to give me a weekly allowance. Each
week he expected me to buy something with my allowance, and each week he
would have me model it for him.
We even stopped at a store in Las Vegas as we were driving to Tucson to let
me start."Here's twenty dollars," he said, "Go buy a skirt and a blouse to
go with it."
It was the scariest thing I'd ever done. Up to that time, everything we'd
done had been in the privacy of our home. This was public. I guess every
cross-dresser remembers her first time buying girl clothes at the store. I
walked around for a while, keeping my eye on the women's section. There
were a few women there, sorting through the racks of clothes. I waited for
them to leave, but no sooner would one leave than two more would show
up. Meanwhile I pretended to be shopping for men's clothing.
Eventually I decided there was never going to be a time when no one else
was there, so I waited until there were only three again, and then went
over to the skirts. By that point I had actually seen something I
liked. Yes, even scared to death like I was, I was looking and thinking. It
was a dark blue skirt, very sporty looking, with thick orange and light
blue stripes that went from the waist to a few inches above the hem, turned
abruptly and wrapped around to the other side.
I picked it up with the hanger, pretty sure it was what I would buy to
satisfy my brother's expectations, when it occurred to me I had no idea
what size skirt I needed. For a moment I froze, panicked. There was really
only one thing I could do, but I had no intentions of doing it there. That
was hold it up to me and measure.
Okay, even doing that, I probably wouldn't know what I was measuring. I
guess hip to hip, but that would have been as much a guess as eyeballing
it. Which is what I finally did. No, I did peek inside at the tag for a
clue. It said, along with washing instructions and what material it was
made of, "M". Whatever that meant. I mean, I knew it meant medium, which
sounded about right. But was medium for girls the same as medium for boys?
Or did I need a large? That's when I eyeballed it. It looked like it would
fit. Plus it had an elastic waist, so I figured I had some leeway. A quick
glance around for another size showed that it was the last one in the store
in that style, and so my mind was made up. I was buying it.
With my face flushed with embarrassment, I went back to men's wear to
figure out what to do about the blouse. I could only wonder how many people
were watching me.
I finally came up with an idea for the blouse. I found a men's shirt that I
knew would fit me, and was roughly something that would look good with the
skirt I was holding, other than the fact that it wasn't meant to be worn
with a skirt. With that as a guide, I went to women's blouses and looked
for something that came close to matching it both in color and size.
That helped, because, with a plan of action, I wasn't as aware of other
shoppers. I was just shopping for something. It could have been for
anybody: my girlfriend, my sister, anyone. Only I knew who it was for, and
that thought aroused me. Not to the point where anything obscene was
showing, but I was definitely turned on by what I was doing.
I finally found a white blouse with cap sleeves that buttoned at the
bottom. It was sheer, but not see-through, and otherwise plain. It wasn't
perfect, by any means, but it seemed to be the same size as the shirt, as
best I could tell, and would satisfy my requirement to Blake. Relieved to
be done, I actually had the presence of mind to return the shirt to where I
had found it, and then hurried to check out.
Shopping got easier after that. Eventually. Being required to do it once a
week – no less often because Blake wanted me to have something to model
for him each week, and no more often because I didn't have the money – I
developed a sense of routine over it. It was still titillating, but not so
much that I couldn't handle it. And by the time I made my second shopping
trip, I knew what sizes I needed.
Sometimes Blake would give me specific assignments for what to
buy. Sometimes he would tell me to buy whatever I wanted. Before long I was
enjoying a large enough wardrobe that I could choose among several outfits
the one I wanted to wear the most.
Modeling the things I bought gave me a sense of confidence in my
femininity. I would start by wearing a complete outfit that included and
highlighted the newest purchases. With a new skirt and blouse or new
nightgown, that was easy enough. But Blake had me start buying jewelry and
even makeup, and that required a little more thought. After walking into
the room, I would stop a few feet in front of him, turn slowly as he
watched, and then walk away again. At the far side of the room I would turn
on the stereo and begin a slow, sexy and seductive strip tease.
It didn't take me long to figure out the best music for stripping, and
eventually I started choosing the music in advance, matching it to the
outfit I was wearing. There was one time when I had purchased a
see-through, snug-fitting body stocking with white hose and garters, so the
song that seemed appropriate was Steppenwolf's "Born To Be Wild".
For my first year of college, I went to school as a boy. After school, as
soon as I got home, I would change into girl things, and spend the rest of
the time that way. Since Blake seldom saw me as anything but a girl, we
decided to give me a girl name. That's when I became Tatum, Blake's very
devoted girlfriend. It seemed like a natural extension of my own name, and
plus it was the name of a young movie actress who was popular at the time.
By the start of my second year of college, Blake assured me I could pass
full time as a girl, and so he had me start going to school that way. By
then I was already making the occasional quick trip to the mailbox or even
to the corner market without bothering to change into boy clothes. It just
started to seem easier and easier to live my life as a girl. And by then I
had really lost any interest I may have had in living my life as a boy.
I got my ears pierced that summer between my first and second years of
college. It just seemed like time. I'd been buying jewelry, but was forced
to buy clip-on earrings, which were painful to wear and were always a joy
to remove. That didn't seem right to me. I wanted to be happy with
everything I was doing as a girl. It was becoming more and more common to
see men with earrings, so, on the surface, I was just following the
trend. In fact, when I got my ears pierced, I was dressed as a boy.
But inside, I knew why I was really doing it, and the real reason was so I
could start buying earrings for pierced ears. They were always cuter and
sexier than the ones I was buying. Not to mention clip-on earrings were
getting harder and harder to find all the time.
At first, Blake and I were content with what we'd been doing all our lives:
oral sex, with me giving and him receiving, kissing and mutual fondling of
one another. But with me spending every night in my brother's bed, and
dressing like a girl for him, it soon reached a point where we needed more.
It happened one night in February, just before Valentine's Day. I had just
bought a few girl clothes, and was modeling them for him. Shopping trips
were still a big adventure for me then, so I was telling him all about it
as I showed him the cute chemise I had bought. It was white with red hearts
all over, and red ruffle trim. Naturally I was wearing it as I showed it to
him, and I told him how I had seen it and just had to have it. So after
passing by it three times in an effort to get up my nerve, I had finally
grabbed it and put it in my basket. With something in my basket, I told
him, it had been easier to stop and sort through a sale on panties, getting
five for eight dollars.
The panties included my first thong panty, a bright red satin thing that
made me feel deliciously sexy as I showed it to him. I could already
imagine myself wearing it to bed later as I sucked his cock.
But Blake had other plans. They still included the blow job, of course;
they just continued on while I was used to that being the end. I had saved
the thong for last in my show that night, realizing it might have some kind
of effect on my older brother. I was submissive, and my brother quite
dominant, but that didn't keep me from occasionally wanting to tempt him.
As expected, Blake responded to the way I was dressed by asking me to come
over and suck his cock. Somewhere we had abandoned the need for games to
initiate sex between us, and living in his apartment it had become a
given. So I knelt between his legs and began sucking him, expecting it to
end the way it usually did, with him cumming in my mouth, and then the two
of us spending the rest of the night in bed together.
But it didn't. After I had sucked him for several minutes, Blake made me
stop. "Go put that mini-skirt on and a bra," he demanded.
I did as I was told, returning a few minutes later wearing the brown
mini-skirt and a plain white bra, since that came the closest to matching
the panties. He looked at me for a while as he slowly played with his hard
dick. I enjoyed, as always, the way it felt when he looked at me. It made
me feel wanted and desirable. He had me turn slowly, seeing me from every
angle.
"Go put on makeup and nylons," he said at length.
That was new, because the usual direction of our sex play was for me to
wear less and less as time went by. "Okay," I said, and went to add the
requested layers.
On a hunch, I added a button-front shirt and hi-heels, since it seemed
Blake wanted to see me fully dressed. I still think that's what he wanted,
and that I saved myself a third trip to add them, even thought the first
thing he said after having me model my outfit was, "Unbutton your shirt one
button at a time and dance for me."
One of Blake's greatest loves is his stereo system. I won't even try to
describe what kind it was. I knew where the on/off switch was, and how to
make it play music I liked, and that the speakers were BIG. Blake would
tell you all about their frequency response and clarity if he was telling
this story and half a dozen other things that would just make my eyes glaze
over if I heard them, but he's not, so you just get my version: It was a
nice stereo.
He put on some soft music and I slowly began dancing and taking my clothes
off for him. We'd come quite a way since "pull down your pants and run."
When I had the shirt off, Blake had me sit on his lap. We'd done that
before, of course, and a few times I had masturbated his cock that way,
using just my bum. I could feel his swollen dick pressing into me from
beneath as I continued to dance.
Meanwhile Blake reached around and played with my titties. I wasn't doing
anything then to make them bigger – I wasn't on hormones or anything -
but I was blessed with natural muscle development there that, with a little
imagination, could make it seem as if I had small A-cup breasts. With his
hard cock pressing into my bum from beneath, and my short skirt up around
my hips, Blake groaned slowly and then said, "I want to fuck you, Tatum."
"Okay."
I suppose in the back of my mind somewhere it occurred to me that I would
eventually need to learn how to do anal. Without a real pussy, it was the
only way I'd ever be able to do anything more than blow jobs. But, to that
point, I hadn't spent a lot of time considering how to do it. The few times
Blake had tried putting his cock inside me had convinced me that I wasn't
ready for it.
Blake, on the other hand, had considered it, and had definite ideas about
the best way to do it. Of course, when Blake decides he wants to do
something, there's very little anyone can do to stop him. And so as I knelt
on the bed, my mini-skirt hiked up to my waist, my thong panty pulled aside
in the back, my face and chest resting on a pillow, I suddenly realized it
was going to happen. Whether I liked it or not.
I decided it made more sense to like it.
Blake had determined that was the best position for first time anal. He
produced a bottle of lube and slathered it over his cock. He then smeared a
generous amount into my crack, using his fingers to push some up inside
me. "It's going to hurt a little at first," he said, "but I'll go slow, and
let you adjust."
"Okay."
"Just tell me when you need me to stop, and then tell me when you're ready
for more." That's about when I realized Blake wasn't going to take no for
an answer. I mean, he would have. He wasn't like that. But I would need to
object pretty strongly, and I had no intentions of objecting, so I knew it
was really going to happen this time. The thought made me shiver with a mix
of delight and dread. What would it feel like to have his cock inside my
ass?
Well, it felt good. Eventually. I'm still amazed at how slowly he went,
never going further than I was ready for, and always stopping when I said
it hurt. "Tell me when you're ready for more," he would say, with half of
his cock buried inside me.
Eventually he had his whole cock inside me. "Is it all the way in?" I
asked.
He reached between us to feel how much was left. "I think that's as far as
I can go," he assured me.
Blake taught me to push back against him, almost as if I was trying to keep
him out. It seemed counter-intuitive, but actually worked to make him go
deeper without causing me too much pain. The pain, as promised, eventually
subsided, and a new feeling took its place. I'll call it lust. I liked how
it felt, to have his cock deep inside me, probing me, filling me. It felt
like a gentle pressure from inside, with waves of pleasure coming from my
anal opening where I could feel his cock slowly moving in and out. "That is
so tight," he said in an awestruck voice. It was his first time too.
We gradually picked up speed as my body adjusted to the intrusion. I could
feel Blake's balls slapping against my crotch. Even now that is the thing I
remember most. It was such an incredible feeling that I suddenly started
cumming, even though I was barely touching my cock at the time.
As I moaned and squirted, my convulsions triggered Blake's cum, and he
shouted, "I'm cumming." I felt his cock twitch inside me. Once, twice,
three times, and then a deep thrust forward.
And that's how I finally became a "real woman".
* * * * *
Of course, there was a lot more. More sex, and more cross-dressing. And
always taking it one step forward all the time.
By the start of my sophomore year I was spending so much time dressed as a
girl that there didn't seem to be a real reason not to attend my classes
that way. Of course I felt obligated to meet with my professors at some
point early in the semester to explain who I was. In most cases they would
give me a quick double-take and then shrug. It was my life. As long as I
met the course requirements, it didn't matter how I wanted to dress.
In my third year of college Blake and I started talking seriously about my
transitioning. He wanted to help me, even though it was going to be very
expensive. Of course, before we could do that, we realized we would have to
tell our parents. By that time I was living pretty much full time as a
woman, but still hadn't told them.
Blake insisted that it wasn't something we could do on the phone, and so I
found myself on a plane, dressed as a woman, with a checked bag that
contained nothing but girl clothes. Whatever our parents reaction, I had no
recourse. I was committed.
Well, other than hurt feelings and dumbfounded silence, they took it pretty
well, I'd say. Mom took it better than Dad. She cried, and hugged me. "Are
you sure this is what you want?" she said.
I assured her it was. What else could I say? Was it really what I wanted?
Even now, I'm not sure how to answer that question. Mostly because I don't
feel it was ever really my choice. It's just something that happened. It's
who I was, and who I am. To try to deny it would have been
pointless. Living my life as a male would only have been frustrating. I'm
happy with the choice, but I honestly feel that I didn't choose it; it
chose me.
Eventually my dad accepted the fact that, whether he liked it or not, he
was going to have two daughters. "I guess I always knew you were going to
be different," he said. And that was about the closest he ever came to
telling me it was okay.
Elise took it very well. "I always wanted a baby sister," she said. Even
though sports had kept her busy all the time we were growing up and had
prevented the two of us from being as close as we otherwise might have
been, transitioning seemed to bring us back together. I called her at least
once a week during my transition – usually more often - and still call
her at least twice a month. Sometimes just to talk, but sometimes for the
kind of help and comfort only another woman can give. She offered me moral
support when I needed it most, and became my very best supporter after
Blake. I honestly don't think I could have made it without her.
I never told her about wearing her clothes.
And we never told our parents about our sexual relationship. They may have
suspected, but they never asked, and we never told them. Eventually Elise
asked me, in confidentiality, if we were having sex. When I said yes, she
said, "I knew it!"
"Shh," I hissed over the phone. "Mom and Dad still don't know."
She assured me our secret was safe with her, but actually seemed quite
pleased with the thought of her brother screwing her new baby sister. "So
how was it your first time?" she asked. And that was the beginning of an
extremely sex-filled conversation.
Eventually I moved out of Blake's apartment and into a place of my own. It
just seemed appropriate. We still got together regularly for sex, but even
that eventually lessened as I started seeing new guys.
But Blake was the one who made everything possible. With his help, I went
through the necessary psychological exams, and started taking hormones. I
remember that very first pill. We decided to throw a small party with a
cake. It was just the two of us, of course, and Blake had the bakery make a
cake with a small pedestal in the center where we placed my very first
"girl pill". When we cut the cake, I got the piece with the pill on it, and
ate it with my cake.
Blake watched me as I swallowed the first of many doses. "Do you feel any
different?" he asked once I had swallowed it.
Of course he supported me through the whole thing. He paid for
everything. I can't begin to say how grateful I am for that. But more than
that he was there for me. Hormones make you moody, and I appreciated his
endless patience very much. On the day I actually went to SRS, he was there
with me, holding my hand as I went in, and there to greet me when I came
out. "Hey girl," he said with a huge smile.
And that's why my brother Blake is just about the coolest brother you could
ever have.